N-bromobutanimide → 1,3-Dibromo-2,4-dimethoxybenzene

HRID 2206822Notes

Reaction equation

HRID 2206822 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[Br:12]N1C(=O)CCC1=O>C(#N)C>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Br:12])[C:3]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 6122962-Bromo-1,3-dimethoxybenzene

Product 1

HCID 116450531,3-Dibromo-2,4-dimethoxybenzeneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

17.9 g of 1-bromo-2,6-dimethoxybenzene and 200 mL of acetonitrile were placed in a flask, and the resulting mixture was cooled on ice. Then, 14.7 g of N-bromosuccinimide was added. Then, while heating the reaction solution to room temperature, stirring was conducted for 8 hours. 2.39 g of N-bromosuccinimide was further added, and stirring was conducted at room temperature for 7 hours. After completion of the stirring, the solvent was distilled off under reduced pressure. Residues were dissolved in dichloromethane, and washed sequentially with sodium thiosulfate and saturated saline. An organic phase was dried with magnesium sulfate and concentrated. Residues were purified by means of silica gel column chromatography, whereby 23.2 g (yield: 95%) of colorless oil of 1,3-bromo-2,6-dimethoxybenzene was obtained.

Workup

  1. temperaturethe resulting mixture was cooled on ice
  2. stirringstirring
  3. waitwas conducted at room temperature for 7 hours
  4. distillationAfter completion of the stirring, the solvent was distilled off under reduced pressure
  5. dissolutionResidues were dissolved in dichloromethane
  6. washwashed sequentially with sodium thiosulfate and saturated saline
  7. dry with materialAn organic phase was dried with magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-30dc6c2b67c34d17b24c05766107cebb
Source dataset
uspto-grants-2016_06
Patent number
US09373792B2

Reaction notes

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